104617-86-9

Basic information

• Product Name: (±)-PraMipexole
• Synonyms: 2-Amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole;Pramipexole Impurity 9
• CAS NO: 104617-86-9
• Molecular Formula: C₁₀H₁₇N₃S
• Molecular Weight: 211.32708
• Mol File: 104617-86-9.mol

Chemical Properties

• Boiling Point: 378°C at 760 mmHg
• Flash Point: 182.4°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 6.49E-06mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated), DMSO (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: (±)-PraMipexole(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-PraMipexole(104617-86-9)
• EPA Substance Registry System: (±)-PraMipexole(104617-86-9)

Safety Data

• Hazardous Substances Data: 104617-86-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(±)-PraMipexole is used as an antiparkinsonian agent for the treatment of Parkinson's disease. It helps alleviate the symptoms of the disease by mimicking the effects of dopamine, a neurotransmitter that is often deficient in Parkinson's patients. This leads to improved motor function and a reduction in the severity of symptoms such as tremors, rigidity, and bradykinesia.
Additionally, (±)-PraMipexole has been found to have potential applications in other areas of medicine, such as the treatment of restless legs syndrome and certain types of depression. However, these uses are still under investigation and may require further research to confirm their efficacy and safety.

InChI:InChI=1/C10H17N3S/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8/h7,12H,2-6H2,1H3,(H2,11,13)

Upstream product

• 123-38-6 propionaldehyde 
• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 
• 104618-25-9 N,N-4-oxocyclohexyl-n-propyl-amine 
• 420-04-2 CYANAMID 
• 873536-19-7 C₉H₁₇NOS 
• 1044921-37-0 4-propanoamidocyclohexanone 
• 1156622-74-0 4-propionamidocyclohexanol 
• 6850-65-3 p-hydroxycyclohexylamine 
• 1026083-71-5 N-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-2,4,6-trimethyl-N-propylbenzenesulfonamide 
• 107-10-8 propylamine 
• 556-53-6 N-propylamine hydrochloride 
• 404892-20-2 2-amino-6-oxo-4,5,6,7-tetrahydrobenzothiazole hydrobromide 
• 113030-24-3 2-amino-6-oxo-4,5,6,7-tetrahydrobenzothiazole 
• 375824-96-7 2-amino-6-(propionylamino)-4,5,6,7-tetrahydrobenzothiazole 

Downstream Products

• 104632-28-2 (R)-(+)-pramipexole 
• 104632-26-0 pramipexole 
• 1612146-41-4 N⁶-(5-(2,5-dimethoxyphenyl)pentyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine 
• 1612146-50-5 (Z)-N⁶-(5-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)pent-4-en-1-yl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine 
• 1612146-60-7 4-(3-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)propyl)-2-methoxyphenol 
• 1612146-68-5 (Z)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pent-1-en-1-yl)-2-methoxyphenol 

Relevant articles and documents

A preparation method of pramipexole hydrochloride (by machine translation)

The invention discloses a method for preparation of pramipexole hydrochloride, comprises the following steps: to amino cyclohexyl [...] acyl chloride condensation for protecting amino group to obtain the propionyl cyclohexanol, then is obtained by catalyt

PROCESS FOR THE PREPARATION OF PRAMIPEXOLE AND NEW ANHYDROUS FORMS OF ITS DIHYDROCHLORIDE

The present invention provides processes for the preparation of (?) pramipexole or an acid addition salt thereof of Formula I. The present invention further provides for the novel polymorphic Forms A and B of anhydrous pramipexole dihydrochloride.

Bioisosteric heterocyclic versions of 7-{[2-(4-phenyl-piperazin-1-yl)ethyl] propylamino}-5,6,7,8-tetrahydronaphthalen-2-ol: Identification of highly potent and selective agonists for dopamine D3 receptor with potent in vivo activity

In the current report, we extend the SAR study on our hybrid structure 7-{[2-(4-phenyl-piperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphthalen- 2-ol further to include heterocyclic bioisosteric analogues. Binding assays were carried out with HEK-29

NOVEL PROCESS FOR SYNTHESIS OF PRAMIPEXOLE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to a novel process for synthesis of pramipexole, shown in the synthesis scheme. Formulae (I), (II), (III), (IV), (V) and (VI).

METHOD FOR THE RESOLUTION OF 2-AMINO-6-PROPYLAMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOL AND INTERMEDIATE COMPOUNDS

The invention relates to a novel method for the resolution of the racemic mixture of compound (R,S)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole, or the enrichment of same with in one of its enantiomers, and to intermediate compounds which can be used to perform said method.

METHOD OF OBTAINING 2-AMINO-6-ALKYL-AMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOLES

The present invention relates to a process for preparing 2-amino-6-alkyl-amino-4,5,6,7-tetrahydrobenzothiazoles (I) wherein the asterisk (*) represents an asymmetric carbon and R1 is C1-C6 alkyl; their enantiomers or mixtu

Novel process for preparing pramipexole and its optical isomeric mixture by reduction with sodium triacetoxyborohydride

A novel process is provided for producing pramipexole base or its optical isomeric mixture as defined hereinabove i.e. (R,S)-2-amino-6-propyl-4,5,6,7-tetrahydrobenzothiazole avoiding the use of borane tetrahydrofuran complex and using a more convenient reducing agent like sodium triacetoxyborohydride instead. The provided process comprises reacting the starting material (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole or its optical isomeric mixture as defined hereinabove i.e. (R,S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole with propionaldehyde in an organic solvent to obtain the respective enamine, which is subsequently reduced in situ, optionally without isolation, to obtain pramipexole or its optical isomeric mixture as defined hereinabove i.e. (R,S)-2-amino-6-propyl-4,5,6,7-tetrahydrobenzothiazole, and the acid addition salts thereof. The present invention also provides a process for purifying pramipexole dihydrochloride or the dihydrochloride salt of its optical isomeric mixture as defined hereinabove i.e. (R,S)-2-amino-6-propyl-4,5,6,7-tetrahydrobenzothiazole dihydrochloride by re-crystallization from a suitable solvent.

PROCESS FOR THE PREPARATION OF PRAMIPEXOLE AND NEW ANHYDROUS FORMS OF ITS DIHYDROCHLORIDE

The present invention provides processes for the preparation of (-) pramipexole or an acid addition salt thereof of Formula I. The present invention further provides for the novel polymorphic Forms A and B of anhydrous pramipexole dihydrochloride.

Process for preparation of 2-amino-6 (alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles

A new process to obtain pramipexole and related products is described. The process involves the reaction of new compounds of formula (6), wherein R is hydrogen or acyl group, R3 and R4 are either the same and each of them represents an alkoxy group of 1-4 carbons or they together form a C2-C5 alkylenedioxy group or an oxo-group, with an alkylamine in the presence of a reducing agent or a hydrogen gas with hydrogenation catalyst. A process to obtain new compounds of formula (6) is also described.

PROCESS FOR THE PREPARATION OF 2-AMINO-4,5,6,7-TETRAHYDRO-6-AMINOBENZOTHIAOLES FROM CYCLOHEXANES AND CYCLOHEXANONES AS INTERMEDIATES

The present invention relates to processes for the preparation of 2-amino-4,5,6,7-tetrahydro-6-aminobenzothiazoles (5a) from cyclohexanes (2a) and cyclohexanones (3a) as intermediate.